Day: April 18, 2022

Application of 1211536-01-4 ,Some common heterocyclic compound, 1211536-01-4, molecular formula is C6H5BrFN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To microwave vial was added 2-bromo-6-fluoro-3-methylpyridine (1355 mg, 7.13 mmol), tert-butyl piperazine-1-carboxylate (1338 mg, 7.18 mmol), anhydrous NMP (3.5 mL), and DIPEA (1.65 ml, 9.45 mmol). The resulting mixture was heated at 120 C for 16 hours. The reaction mixture was allowed to cool to room temperature. The mixture was then diluted with EtOAc (100 mL), washed with water (20 mL) and brine (20 mL), dried over sodium sulfate, filtered and concentrated. The crude residue was purified by flash chromatography (80 g Si02, 0-25% EtOAc in hexanes) to afford tert-butyl 4-(6-bromo-5-methylpyridin-2-yl)piperazine-1- carboxylate (46-1) as a waxy tan solid. HRMS m/z (M+H) 356.0971 measured, 356.0968 calculated.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1211536-01-4, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LAYTON, Mark, E.; KELLY, Michael, J.; HARTINGH, Timothy, J.; WO2011/109277; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 824-52-2, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 824-52-2, name is 5-Methyl-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

b) 5-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde can be prepared as follows: Add 1.6 g of 1,3,5,7-tetraazatricyclo[3.3.1.1~3,7~]decane to a suspension of 1 g of 5-methyl-1H-pyrrolo[2,3-b]pyridine in a mixture of 10 cm3 of water and 5 cm3 of acid acetic. Reflux the mixture under argon for four hours and thirty minutes, then add 30 cm3 of water to the hot mixture and leave to return to room temperature while stirring overnight. Then extract the mixture with three times 50 cm3 of ethyl acetate. Then combine the organic phases and wash with 3 times 50 cm3 of water, dry over magnesium sulphate and concentrate to dryness at reduced pressure to obtain 610 mg of a mixture containing 65% (by NMR) of 5-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde in the form of a yellow powder, for which the characteristics of the main product are as follows:

According to the analysis of related databases, 824-52-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; sanofi-aventis; US2009/253679; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 884494-45-5, Adding some certain compound to certain chemical reactions, such as: 884494-45-5, name is 2-Fluoro-4-iodo-6-methylpyridine,molecular formula is C6H5FIN, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 884494-45-5.

INTERMEDIATE 24 4-lodo-A/,6-dimethvlpyridin-2-amine A stirred mixture of 2-fluoro-4-iodo-6-methylpyridine (0.30 g, 1.3 mmol), triethylamine (0.53 mL, 3.8 mmol) and methylamine (2 M in THF, 2 mL, 4.0 mmol) in NMP (3 mL) was heated at 160 C for 18 h. The reaction mixture was allowed to cool to ambient temperature, concentrated in vacuo and purified by reversed-phase HPLC on a C-18 column, eluting with a gradient of H20:CH3CN:TFA – 95:5:0.1 to 5:95:0.1, to give the title compound. MS: m/z = 249.0 (M + 1). 1H NMR (400 MHz, DMSO) delta 7.22 (s, 1H), 7.06 (s, 1H), 2.89 (s, 3H), 2.54 (s, 1H), 2.35 (s, 3H).

According to the analysis of related databases, 884494-45-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BELL, Ian, M.; ZHAO, Lianyun; FRALEY, Mark; ZHU, Cheng; BIFTU, Tesfaye; BRNARDIC, Edward Joseph; WANG, Cheng; ZARTMAN, C. Blair; GALLICCHIO, Steven; NGUYEN, Diem; CROWLEY, Brendan; POTTEIGER, Craig; (257 pag.)WO2016/22644; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 15862-50-7, name is 3-Bromo-2-methoxy-5-nitropyridine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 3-Bromo-2-methoxy-5-nitropyridine

Example 1.1: Preparation of Intermediate 2-Methoxy-3-(2-methyl-2H~pyrazol-3-yl)-5- nitro-pyridine.To a suspension of 3-bromo-2-methoxy-5-nitrorhoyridine (986 mg, 4.23 mmol), 1- methyl-lH-pyrazol-5-ylboronic acid (1.55 g, 12.3 mmol), and CsCO3 (5.24 g, 16.1 mmol) in DME (80 mL) under argon was added Pd(PPh3),, (269 mg, 0.233 mmol). The reaction mixture was heated to 85C overnight, cooled to room temperature, and then diluted with water (250 mL) and extracted with ethyl acetate (250 mL). The organic layer was dried with MgSO4 and concentrated in vacuo. The resulting residue was purified by HPLC to afford 2-methoxy-3-(2- methyl-2H-pyrazol-3-yl)-5-nitro-pyridine as a beige solid (312 mg, 31%). LCMS m/z (%) = 235 (M+H, 100). 1H NMR (400 MHz, DMSO-d6) delta: 9.20 (d, J= 2.76 Hz, IH), 8.47 (d, J= 2.76 Hz, IH), 7.53 (d, J= 1.90 Hz3 IH), 6.48 (d, J= 1.87 Hz, IH), 4.05 (s3 3H), 3.72 (s, 3H).

The synthetic route of 15862-50-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2007/120600; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 71670-70-7, name is 2-(Chloromethyl)-5-methylpyridine hydrochloride. A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(Chloromethyl)-5-methylpyridine hydrochloride

EXAMPLE 10 Preparation of 1,5,6,7-tetrahydro-2-[[(5-methyl-2-pyridyl)methyl]thio]indeno(5,6-d)imidazole To 13.5 g of 1,5,6,7-tetrahydroindeno(5,6-d)imidazole-2-thiol, suspended in 200 ml of alcohol, were added dropwise while stirring 5.9 g of sodium hydroxide in 100 ml of water and, after 30 minutes, 13.0 g of 5-methyl-2-chloromethyl-pyridine hydrochloride were added. The mixture was left to boil at reflux overnight, then evaporated and the residue was taken up in methylene chloride. This was washed neutral and, after drying over sodium sulfate, evaporated in vacuo. The residue, recrystallized from acetonitrile, gave 11.9 g (56.9% of theory) of 1,5,6,7-tetrahydro-2-[[(5-methyl-2-pyridyl)methyl]thio]indeno(5,6-d)imidazole of melting point 157-158 C. The mother liquor was evaporated, the residue was dissolved while heating in methanol, and the solution was treated with 5 N hydrochloric acid in ethyl acetate.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 71670-70-7, 2-(Chloromethyl)-5-methylpyridine hydrochloride.

Reference:
Patent; Hoffmann-La Roche Inc.; US4435406; (1984); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 169205-95-2, Adding some certain compound to certain chemical reactions, such as: 169205-95-2, name is 2-(Methylthio)oxazolo[4,5-b]pyridine,molecular formula is C7H6N2OS, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 169205-95-2.

A solution of 116A (8g, 47.6 mmoi) and 116B (5g, 30 mmol) in DMF was heated at 100 C for overnight. The reaction mixture was concentrated under vacuum and purified by column chromatography to give 116 as syrup (9 g, 99%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 169205-95-2, 2-(Methylthio)oxazolo[4,5-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SCHERING CORPORATION; PALANI, Anandan; RAO, Ashwin, U.; CHEN, Xiao; SHAO, Ning; HUANG, Ying, R.; ASLANIAN, Robert, G.; WO2010/71819; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 832715-99-8 , The common heterocyclic compound, 832715-99-8, name is 6-(tert-Butyl)nicotinic acid, molecular formula is C10H13NO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Step 3: Preparation of (R)-2-(3-(6-tert-butylnicotinamido)piperidin- 1 -yl)-5-(pyridin-2- ylamino)thiazole-4-carboxamide To a solution of 6-tert-butylnicotinic acid (23.5 mg, 131 imol) and 2-((R)-3-amino-piperidin-1-yl)-5-(pyridin-2-ylamino)-thiazole-4-carboxylic acid amide (38 mg, 119 imol) in N,Ndimethylformamide (1 mL) was added diisopropylethylamine (35 tL, 200 imol) followed by 0- (benzotriazol- 1 -yl)-N,N,N?,N?-tetramethyluronium hexafluorophosphate (61 mg, 161 imol). After stirring at ambient temperature overnight under an atmosphere of argon the reaction was quenched by the addition of saturated aqueous ammonium chloride (2 mL), the mixture pouredinto water (5 mL) and extracted with ethyl acetate (3 x 3 mL). The combined organic extracts were washed with brine (2 x 2 mL), dried over sodium sulfate, filtered and concentrated in vacuo to a yellow solid. The crude product was purified by chromatography using a 13 g C-18 column gradient eluted from 10% acetonitrile in water up to 100% acetonitrile. The product containing fractions were combined and concentrated in vacuo and the residue lyophilized from acetonitrile / water to give (R)-2-(3-(6-tert-butylnicotinamido)piperidin- 1 -yl)-5-(pyridin-2-ylamino)thiazole- 4-carboxamide as a pale yellow solid (37.8 mg, 66 %).LC/MS: mlz calculated for C24H29N702S ([M+Hj): 480.6. Found: 480.3 (positive modeelectrospray ionization).

The synthetic route of 832715-99-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HUBY, Nicholas John Silvester; LOPEZ-TAPIA, Francisco Javier; SO, Sung-Sau; WO2014/90715; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1062368-71-1, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 1062368-71-1, name is Methyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

A solution of methyl 4-bromopyrazolo [1 ,5-ajpyridine-3-carboxylate (500 mg, 1.97 mmol), potassium trifluoro(2-methoxyethyl)borate (490 mg, 1.28 mmol), RuPhos (734 mg, 1.58 mmol), Pd(OAc)2(177 mg, 0.79 mmol) and C52CO3(1.92 g, 5.91 mmol) in CPME (8 mL) and water (2 mL) was stirred for 5 hours at 100 C under N2. The mixture was diluted with water,extracted with EA(x3), the organic layer was dried, concentrated. The crude product was purified via silica gel chromatography (PE-EA) to give desired compound as yellow solid (140 mg, 30%). ESI MS m/z = 235.3 [M+Hf.

According to the analysis of related databases, 1062368-71-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; SHOOK, Brian, C.; KIM, In, Jong; BLAISDELL, Thomas, P.; YU, Jianming; PANARESE, Joseph; OR, Yat, Sun; (434 pag.)WO2017/15449; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1019021-85-2 ,Some common heterocyclic compound, 1019021-85-2, molecular formula is C8H5FN2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To a solution of 6-fluoroimidazo[1 ,2-a]pyridine-3-carboxylic acid (13a) (210 mg, 1 .2 mmol) in dichloromethane (8 mL) was added oxalyl chloride (250 muIota, 2.8 mmol) and DMF ( 40 muIota) at 0-10 C. The resulting solution was stirred 30 min at room temperature and concentrated under vacuum. A solution of 3-amino-4-fluoro-N-((1 R,2S)-2-hydroxy-2,3- dihydro-1 H-inden-1 -yl)benzamide (16) (350 mg, 1 .2 mmol) in 3 mL of pyridine was added into the above obtained solid. The resulting solution was stirred 30 minutes at room temperature The above solution was purified by preparative mass trigger LCMS to afford N-(2-fluoro-5-(((1 R,2S)-2-hydroxy-2,3-dihydro-1 H-inden-1 -yl)carbamoyl) phenyl)- 6-fluoroimidazo[1 ,2-a]pyridine-3-carboxamide (F27) as a light yellow solid. 1 H NMR (400MHz, d6-MeOH) delta 9.57 (dd, J = 4.8, 2.4 Hz 1 H), 8.60 (s, 1 H), 8.35 (dd, J = 7.2, 2.4 Hz, 1 H), 7.80-7.85 (m, 2H), 7.65-7.71 (m, 1 H) 7.18-7.37 (m, 5H), 5.54 (d, J = 5.2 Hz, 1 H), 4.65 (td, J = 8.4, 2.0 Hz, 1 H), 3.18 (dd, J = 16, 5.2 Hz,1 H), 2.97(dd, J = 16.4, 2.0 Hz, 1 H). (MS m/z 449.1 (M+1 )+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1019021-85-2, its application will become more common.

Reference:
Patent; IRM LLC; NOVARTIS PHARMACEUTICALS UK LIMITED; LIANG, Fang; GIBNEY, Michael; YEH, Vince; LI, Xiaolin; MOLTENI, Valentina; SHAW, Duncan; BERMAN, Ashley Mitchell; LEWIS, Sarah; LOREN, Jon; FURMINGER, Vikki; WO2013/33620; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine, molecular formula is C6H5F3N2, molecular weight is 162.11, as common compound, the synthetic route is as follows.name: 5-(Trifluoromethyl)pyridin-3-amine

To a solution of 5-(trifluoromethyl)pyridin-3-amine (3 g) in 6N hydrochloric acid (30 mL) was added a solution of sodium nitrite (1.277 g) in water (15 mL) dropwise over 2 minutes at 0 C. The reaction mixture was stirred at 0 C. for 1 hour. To the reaction mixture was added a suspension of tin (II) chloride (8.77 g) in 6N hydrochloric acid (30 mL) dropwise over 3 minutes at 0 C. The reaction mixture was stirred at 0 C. for 28 minutes and at room temperature for 20 hours 9 minutes. To the reaction mixture was added 8N aqueous sodium hydroxide solution (about 68 mL) dropwise at 0 C. The mixture was stirred at 0 C. The mixture was extracted three times with ethyl acetate. The obtained organic layers were combined, washed with brine, dried over sodium sulfate, and concentrated. To the resulting residue was added a seed crystal of the title compound separately synthesized in a similar manner to this step. To the mixture was added a mixture of diisopropylether (2 mL)/n-hexane (30 mL) at room temperature. The suspension was stirred at room temperature. The solid was collected from the suspension by filtration and washed with n-hexane. The solid was dried under reduced pressure at room temperature to give the title compound (2.8464 g) in 87% yield. (0291) 1H-NMR (CDCl3) delta: 3.69 (br s, 2H), 5.49 (br s, 1H), 7.43-7.45 (m, 1H), 8.28-8.30 (m, 1H), 8.34 (d, 1H, J=2.8 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,112110-07-3, 5-(Trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; Japan Tobacco Inc.; MIURA, Tomoya; HIRASHIMA, Shintaro; MANABE, Tomoyuki; IIDA, Tetsuya; SAKURAI, Kentaro; (53 pag.)US2019/330193; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem